Water → [4-methyl-1-(propan-2-yl)-1H-imidazol-5-yl]methanol
Reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH:9]([CH3:11])[CH3:10])[C:6]=1[CH:7]=[O:8].[BH4-].[Na+].O>CO>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH:9]([CH3:11])[CH3:10])[C:6]=1[CH2:7][OH:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 0° C. solution of 4-methyl-1-(propan-2-yl)-1H-imidazole-5-carbaldehyde (924 mg, 6.1 mmol) in anhydrous methanol (75 mL) was added sodium borohydride (425 mg, 11.2 mmol). The reaction mixture was stirred at room temperature for 3 hours. Water (20 mL) was added. Methanol was evaporated. The resultant mixture was extracted with EtOAc (1×20 mL) and 2-butanol (2×20 mL). The solution was dried over MgSO4, filtered, evaporated, and dried in vacuo, affording [4-methyl-1-(propan-2-yl)-1H-imidazol-5-yl]methanol (703 mg, 75% yield). The product was used without further purification.
Workup
- customMethanol was evaporated
- extractionThe resultant mixture was extracted with EtOAc (1×20 mL) and 2-butanol (2×20 mL)
- dry with materialThe solution was dried over MgSO4
- filtrationfiltered
- customevaporated
- customdried in vacuo
Sources & evidence
- ORD record
- ord-20f7fcfd8ec0480db29a3a0f46aca30d
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040538B2
Reaction notes
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